1,509 results for sissy training

Zoey




Welcome to your new obsession in online sissy training. You are now in submissive service to Miss Zoey. The hot daddy cock tease and a size queen. You will pay to play and if that dick doesn’t measure up I will make you my slutty girlfriend no questions asked! We will do everything girls do together as I take control of every inch of your body. I live for slutty sissys’ and small dicked cuckolds to keep as my puppy pet on my leash. Wouldn’t you enjoy watching me get fucked? I will walk all over you in spiked stilettos and still deny you entrance into my sweet tight cunt!. I’m not a princess but I can make you into one as you shell out your hard earned money to buy me some Dior Addict lip gloss! Don’t worry if you’re a really good boy you can try some on too! Maybe you are in denial of what you really are and require a little forced sissy training. That is something I adore about shy sissy wannabes. You need to be forced to wear a cock cage and denied orgasm as you perform menial tasks! I want to introduce you to a plethora of cock. Step by sissy step you will rely on me for all pleasure. I will become your obsession. I have rules that if broken require punishment physical and verbal! Do not cross me, I can be a kind and loving Slave trainer or a dominatrix it is all up to how good you obey me. As your mistress will dress you up pretty in your panties and stockings and sissy dresses as we go through all of our online sissy training together. I enjoy cock worship, Sissy dress up time and even forced cum eating. And don’t forget about edge play and erotic hypnosis fun!

Violet



I grew up in a small town where you remain a virgin until you marry your high school sweetheart and live a happily ever after life. Unfortunately, that fairy tale was just that, a mirage, a work of fiction. I married the star quarterback, a tall, built, chiseled, hunk of a man only to find out on our wedding night that he has a tiny dick that even my virgin hole could not feel when he stuck it in me. He would never be able to satisfy me. Not long after, we moved to a bigger city where he became one of the most powerful men. Alone in this new town, I found myself in an affair with a man who had a nice big dick. I liked how it felt, I liked how he pounded me, I liked the orgasms. With my husband’s position I couldn’t divorce him so what did I do? I made him my little sissy bitch with some sissy phone sex. You see this powerful man, but what you don’t know is that he is wearing his little sissy panties under his suit. Sometimes I even make him wear a bra and thigh high stockings. He knows he can’t satisfy me, so he is now my sissy maid to do whatever I want whenever I want. I have made him a cuckold, making him watch as I fuck every man in town. I often let my guests fuck him in his little man pussy as I film it, so I always have a little blackmail tape, just in case. I joined a woman’s group and a few of the girls have sent their husband’s my way so that I can make them little sissies too. I now spend my days fucking whomever I want and training these little sissy girls to be obedient, to wear panties and all things frilly and to do exactly what I tell them to do. I would love to give you online sissy training so that you too can be my little sissy bitch.

Tanya



I’m a tough bitch, and I’m going to make you the best fucking sissy around! If you’re a little whiny ass bitch boy who needs a real Mistress to put you in your place, you found her. Look no farther, I got your fucking number, tiny dick! I’m a dominant, forceful Mistress and demand obedience and perfection from all my little fag boys. I’ll dress you in leather and lace and doll you up, in excellence. When we go out no one will suspect you’re not a real woman when I’m done with you. And no one will know our little secret, as long as you do what you’re told. You are mine now and you well do whatever I say, and don’t you fucking forget it. I’ll take you out and show you off. You’ll have every man in the club eating out of your hands and every woman wishing she was you. You just remember your place as my little fluffer and clean up boy, at first. If you’re a good boy and make it passed the first phase of training, you’re going to love phase two. This is when I send your hot to trot ass out alone, to bring back your stud for the night. You won’t know it, but I’ll be watching, to make sure you do a good job pleasing your bull. Now that I have you under my control and you know that little clit and boy pussy belong to me. You will be my sex slave bringing home all our fuck toy. No, you won’t be fucking me with that little needle dick, but there’s more to being my sex slave than fucking me. You’ve finally graduated and now you are a true sissy slut and you’re loving life in your newfound femininity. But never forget I made you and I can destroy you just as fast. So, make sure you never disappoint or disobey your bitch of a Mistress. It will come back to bite you in your ass.

My specialties include but are never limited to

  • CBT
  • Small Penis Humiliation
  • Forced Bisexuality
  • Forced Sissification
  • Sissy Training
  • Domination 

Emerson




Online sissy training can make or break you. Breaking a man by turning him into a panty-wearing cum eating, cock sucking slut is my ultimate goal! You will worship my perfect female form and lust to be just like me by the time I am done with you! It’s about time you had a Goddess to worship! Grab your AMEX and go shopping with me and for me! We both know that a well-dressed bitch gets the most cock. Spoil me as I humiliate you in public places! Every sissy whore I have ever trained knows he must pay tribute to the woman that gives him his deep-buried feminization! You will begin to crave my voice and skills as a cross-dressing expert. My goal is to break you. It’s for your own good. I promise! If you dare buck back against me, I will use forced feminization to have your ass pussy bucking on cock as fast as you can say cock cage! I will have you addicted to being a complete sissy whore who brings me bull cock to fill my pretty pussy up with hot creamy cum. Cum that you will slurp out of my Size queen pussy! I only fuck and suck cock that is long, strong, and thick! I have sissy lessons that must be completed beforehand though. My holes and house will be cleaned by a pretty sissy maid slave. I learned early in my fuck career that small cock men are only useful if they are my slaves. Speaking of, sissy humiliation training is a passion of mine. I must break your thoughts of you ever being a man in order to bring you into sissy space. This blonde sexy Mistress awaits your dedication. Bring your toys and panties to play with me!

Rosemary




Not all sissy phone sex is the same, some Mistresses are easy going, kind and patient and even sweet but I am not like that at all. I am a harsh Mistress and I expect to be obeyed no matter what. If I give you an order you must comply, even if it embarrasses you, even if you are humiliated and mocked, you must comply or you will never get to gaze as the beauty and perfection that is me. I know everything about you already and we’ve never even spoke. I know that you are a wimpy little sissy bitch with a tiny little peepee. I know that you love women’s clothes even if you won’t admit it. I know that some of you will require forced sissy training even though just hearing the word sissy gets your little clitty rock hard. I will train you to be the perfect little sissy bitch. By the time I am thru with you, you will be an eager little sissy slut sucking and fucking with the best of them. If you are a disobedient little whore, well then you will be punished. I will humiliate you and send you out in public to be found out. I will tell your secret to the world and there will be nothing you can do about it. Are you going to be my good little sissy slut? Or a naughty whore that needs to be punished?

Raine




My days started as a high class escort for high powered corporate CEOs. You’d be surprised to know how many on the Forbes 500 are little fucking sissies bitches. In fact, when I learned about this, I decided to make a slight career change and out my time and energy into becoming a high class sissy fag trainer! Even the clients that claimed they weren’t little faggots, I made sure that they were forcefully feminized. I took sadistic pleasure in turning them from wolves of wall street to girly fags! I became such a great sissy training escort, that I soon had my own harem of little faggots. Nothing gets me going like pathetic small cocks in cum filled lace silk panties. All my sissies wait on me hand and foot in the girliest faggy maid uniforms that money can buy. A spoiled bitch mistress like me loves having powerful business men on their hands and knees dressed up like sniveling sissy whores begging for cum- the irony makes my bald wet pussy so fucking wet! Believe me, I get the best pleasure out of turning grown men into little bitch sissy fags that love to be my personal fuck slaves and cum dumpsters! These whores love having their boy pussies poked and prodded with cocks while I make them worship my feet!

Odessa




I love sissy phone sex. It gives me great joy to feminize a tiny dick loser and turn him into my personal sissy slave. A sexy bitch like me can never have too many handmaids! I am a high-end escort. That is how I got into training sissies. I assumed that men with money and power, who could afford my services, would have big cocks also. That is not always the way it is, however. I am all about earning money, but a sexy babe needs standards too. I don’t care if you have millions of dollars. You can’t fuck me with a Ken Doll package. I demand and deserve the best. You can, however, pay me for some online sissy training if you got money but no dick! I have plenty of sugar daddy sissies, so you would not be alone. I am not cheap, but I am worth every penny. I will dress you up head to toe. I will teach you to suck cock. I will let you do things for me like clean my house, run my errands and eat my creampies. I know how to make you look pretty. And, if you run out of money to pay me for my time, I will pimp you out. I know lots of wealthy real men who will pay good money to test out one of my sissy creations. You are just a sissy living in my sissy world.

Jackie




I know you’re here looking for a sissy training Mistress. I think your search can end here because I’m perfect for turning you into the woman you’ve always wanted to be. I understand that there are different kinds of sissies and I will listen to you and together we will figure out the perfect plan to feminize you.
If you’re the kind of sissy who is only interested in wearing frilly and girly things, I can help you accomplish that. But it will take a little bit of work before we can get to the dressing up part. You’ll have to wax your body, learn to apply make-up, and of course you’ll need to learn how to dress. You will also need to find a wig that will make you look your most beautiful.
And if you would like to eventually become totally feminized and learn to suck and fuck, well, I’m ready to train you for that, too. There isn’t a better woman alive to help you learn to suck cock. I have taught many sissies to please a man and when they are finished with my sissy training, they are the best of the best. Oh, and don’t you worry – I’ll make sure you train your sissy hole to take a big fat cock.
Training begins as soon as you pick up that phone.

Gypsy




I love being a sissy phone sex trainer. I have always been a dominant woman. I was raised to be a proud and strong Hispanic woman. My mother is white, my father is Hispanic. My mom was married before my dad to a loser white man. She cuckolded him and ended up marrying the bull her ex-husband found to spice up their sex life. I am glad he did that, or I never would have been born. My mother is a dominant woman. She cuckolded and pegged her ex-husband. When my Hispanic bull daddy came into her life, she finally found what was missing in her marriage: love and a big thick cock. When I came around, she told me white men would try to disrespect me, so I needed to be bold and stand up to them. I was making boys cry when I was a schoolgirl. In high school, I started pegging high school jocks and feminizing them. None of them ever measured up. When I went to college, I became a professional dominatrix and sissy trainer. I was born to put men in their place. I am still a professional dominatrix, but I supplement my income with online sissy training too. I am strong. I am beautiful. And I am in charge. Try to racially humiliate me, and you will never sit right again. You will address me as Goddess or Mistress. I will never let you fuck me. Like my mother, I am all about strong beautiful dark men. You are my pathetic sissy, femboy, cuckold or slave. Realize that, then we can play.

Genesis




Ever since I was a little girl I have always known what I wanted and knew how to achieve my goals in life.  I am a power-hungry woman who conquers everything I put my fingers on.  I have recently gotten a new goal in life.  I am a dominate I always have been that is why I always accomplish my goals. Well, now my goal is to conquer men and bring them to their knees as the little pathetic creatures they truly are.  I started out with having sissy phone sex with “men” (and I use that term loosely) because I am in control and he is the boi at my feet worshiping every inch of my sexy dominate body.    This came very easy to me and I excelled very quickly but this still was not enough for my appetite.  Men over the phone are easy to control I needed to step up my game if I truly wanted to conquer all men.  I found sissies over the internet who wanted a Mistress.  I have them come to my place and they quickly fall in line giving in to each of my demands.  But again I was still not satisfied there was still something missing.  That is when it hit me almost like a light bulb going off in my head.  What I really needed to be doing was dominating the men that are dominate themselves.  A sissy wants to be a bitch that is where my lack of satisfaction was coming from.  That is when I got into forced sissy training.  I took dominate men and made them sissy bitches under my feet.